MX2013014234A - Metodo para reducir la contaminacion durante la purificacion de esteres de met (acrilato). - Google Patents

Metodo para reducir la contaminacion durante la purificacion de esteres de met (acrilato).

Info

Publication number: MX2013014234A
Authority: MX; Mexico
Prior art keywords: meth; acrylic acid; biacetyl; stream; acid ester
Prior art date: 2011-06-03

Application number

MX2013014234A

Other languages

English (en)

Spanish (es)

Inventor

Michael A Curtis

Michael Stanley Decourcy

David A Flosser

Melissa Harris

Jamie J Juliette

Philippe P Maillot

Original Assignee

Rohm & Haas

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2011-06-03

Filing date

2012-06-01

Publication date

2014-01-23

2012-06-01 Application filed by Rohm & Haas filed Critical Rohm & Haas

2014-01-23 Publication of MX2013014234A publication Critical patent/MX2013014234A/es

Links

238000000034 method Methods 0.000 title claims abstract description 127
238000000746 purification Methods 0.000 title claims abstract description 82
150000001252 acrylic acid derivatives Chemical class 0.000 title description 2
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims abstract description 265
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 155
150000004984 aromatic diamines Chemical class 0.000 claims abstract description 119
230000008569 process Effects 0.000 claims abstract description 64
238000000926 separation method Methods 0.000 claims abstract description 58
238000002156 mixing Methods 0.000 claims abstract description 35
239000011343 solid material Substances 0.000 claims abstract description 27
238000009825 accumulation Methods 0.000 claims abstract description 24
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 123
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 67
238000004821 distillation Methods 0.000 claims description 60
150000002148 esters Chemical class 0.000 claims description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 24
238000011144 upstream manufacturing Methods 0.000 claims description 21
150000004982 aromatic amines Chemical class 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 10
230000003247 decreasing effect Effects 0.000 claims description 9
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 8
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
238000012544 monitoring process Methods 0.000 claims description 8
230000007423 decrease Effects 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
230000003068 static effect Effects 0.000 claims description 3
125000005397 methacrylic acid ester group Chemical group 0.000 claims 3
238000004519 manufacturing process Methods 0.000 abstract description 29
239000007787 solid Substances 0.000 abstract description 8
238000007792 addition Methods 0.000 description 59
238000012360 testing method Methods 0.000 description 37
238000011109 contamination Methods 0.000 description 34
239000000047 product Substances 0.000 description 32
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 26
239000012535 impurity Substances 0.000 description 20
230000035508 accumulation Effects 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 15
239000012530 fluid Substances 0.000 description 15
-1 for example Substances 0.000 description 13
239000003112 inhibitor Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
238000009835 boiling Methods 0.000 description 11
238000001514 detection method Methods 0.000 description 8
238000005886 esterification reaction Methods 0.000 description 8
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 7
230000032050 esterification Effects 0.000 description 7
238000012546 transfer Methods 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 5
230000002441 reversible effect Effects 0.000 description 5
238000003756 stirring Methods 0.000 description 5
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
230000000670 limiting effect Effects 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
238000005070 sampling Methods 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000002245 particle Substances 0.000 description 3
230000000737 periodic effect Effects 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
230000008901 benefit Effects 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000010586 diagram Methods 0.000 description 2
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000446 fuel Substances 0.000 description 2
230000007774 longterm Effects 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000005395 methacrylic acid group Chemical group 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000002699 waste material Substances 0.000 description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
230000000739 chaotic effect Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
230000001066 destructive effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000005553 drilling Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000005189 flocculation Methods 0.000 description 1
230000016615 flocculation Effects 0.000 description 1
239000012634 fragment Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
230000005484 gravity Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
239000003129 oil well Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
229920000247 superabsorbent polymer Polymers 0.000 description 1
239000004583 superabsorbent polymers (SAPs) Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

MX2013014234A 2011-06-03 2012-06-01 Metodo para reducir la contaminacion durante la purificacion de esteres de met (acrilato). MX2013014234A (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US201161492960P	2011-06-03	2011-06-03
PCT/US2012/040349 WO2012167005A1 (fr)	2011-06-03	2012-06-01	Procédé de réduction de l'encrassement pendant la purification des esters (méth)acrylates

Publications (1)

Publication Number	Publication Date
MX2013014234A true MX2013014234A (es)	2014-01-23

Family

ID=46317500

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
MX2013014234A MX2013014234A (es)	2011-06-03	2012-06-01	Metodo para reducir la contaminacion durante la purificacion de esteres de met (acrilato).

Country Status (10)

Country	Link
US (1)	US20140200366A1 (fr)
EP (1)	EP2714642A1 (fr)
JP (1)	JP2014520102A (fr)
KR (1)	KR20140025506A (fr)
CN (1)	CN103596916A (fr)
BR (1)	BR112013030770A2 (fr)
MX (1)	MX2013014234A (fr)
SG (1)	SG195081A1 (fr)
TW (1)	TWI433836B (fr)
WO (1)	WO2012167005A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3333150B1 (fr) *	2015-08-07	2020-09-16	Daikin Industries, Ltd.	Procédé de purification d'un dérivé d'acide acrylique
CN105968012B (zh) *	2016-07-04	2019-11-08	江苏斯尔邦石化有限公司	一种mma洗涤塔酸度消除方法及用于该方法的装置
CN114163329A (zh) *	2021-12-16	2022-03-11	浙江汉景环保化学材料科技有限公司	一种防污剂

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4668818A (en)	1985-06-18	1987-05-26	E. I. Du Pont De Nemours And Company	Methyl methacrylate production
US5571386A (en)	1994-05-31	1996-11-05	Rohm And Haas Company	Process for grade acrylic acid
FR2721923B1 (fr) *	1994-06-30	1996-08-14	Atochem Elf Sa	Procede de fabrication de methacrylate de methyle sans diacetyle
US5961790A (en)	1994-12-14	1999-10-05	Basf Aktiengesellschaft	Separation of (meth) acrylic acid by rectification
JP2001288147A (ja) *	2000-04-11	2001-10-16	Mitsubishi Rayon Co Ltd	メタクリル酸メチルの精製方法
WO2012060990A1 (fr) *	2010-11-04	2012-05-10	Rohm And Haas Company	Procédé de production de méthacrylate de méthyle ayant une teneur en biacétyle réduite

2012
- 2012-05-30 TW TW101119281A patent/TWI433836B/zh not_active IP Right Cessation
- 2012-06-01 CN CN201280027197.7A patent/CN103596916A/zh active Pending
- 2012-06-01 EP EP12727969.3A patent/EP2714642A1/fr not_active Withdrawn
- 2012-06-01 SG SG2013086103A patent/SG195081A1/en unknown
- 2012-06-01 JP JP2014513724A patent/JP2014520102A/ja active Pending
- 2012-06-01 US US14/119,904 patent/US20140200366A1/en not_active Abandoned
- 2012-06-01 BR BR112013030770A patent/BR112013030770A2/pt not_active IP Right Cessation
- 2012-06-01 KR KR1020137032112A patent/KR20140025506A/ko not_active Withdrawn
- 2012-06-01 WO PCT/US2012/040349 patent/WO2012167005A1/fr not_active Ceased
- 2012-06-01 MX MX2013014234A patent/MX2013014234A/es unknown

Also Published As

Publication number	Publication date
US20140200366A1 (en)	2014-07-17
SG195081A1 (en)	2013-12-30
CN103596916A (zh)	2014-02-19
KR20140025506A (ko)	2014-03-04
TW201309638A (zh)	2013-03-01
BR112013030770A2 (pt)	2016-12-06
JP2014520102A (ja)	2014-08-21
EP2714642A1 (fr)	2014-04-09
WO2012167005A1 (fr)	2012-12-06
TWI433836B (zh)	2014-04-11

Publication	Publication Date	Title
US7253307B1 (en)	2007-08-07	Process for production of methacrylic acid
JP4850190B2 (ja)	2012-01-11	水分含量が低減された（メタ）アクリル酸の製造プロセス
KR101994630B1 (ko)	2019-07-02	온라인 근적외선 분석을 이용한 (메트)아크릴산 정제 방법의 제어
KR102698594B1 (ko)	2024-08-23	폴리머 등급의 (메트)아크릴산의 개선된 제조 방법
MX2013014234A (es)	2014-01-23	Metodo para reducir la contaminacion durante la purificacion de esteres de met (acrilato).
CN101205196A (zh)	2008-06-25	丙酮合氰化氢的蒸馏处理以及制备甲基丙烯酸酯和后续产物的方法
TWI496768B (zh)	2015-08-21	抑制（甲基）丙烯酸及／或（甲基）丙烯酸酯之聚合反應之方法
US20080021241A1 (en)	2008-01-24	Process for production of methacrylic acid
KR101439573B1 (ko)	2014-09-11	알킬 메타크릴레이트의 흡착 정제 방법
US7188639B2 (en)	2007-03-13	Storage tank for easily polymerizable compound and method of storage
CN104024208A (zh)	2014-09-03	甲基丙烯酸的精制方法
CN103848735A (zh)	2014-06-11	复合阻聚剂在丙烯酸精制过程中的应用
JP2021155452A (ja)	2021-10-07	（メタ）アクリル酸の製造方法
CN104768920B (zh)	2017-03-08	由丙酮氰醇和硫酸生产mma和/或maa的方法
WO2017110506A1 (fr)	2017-06-29	Procédé de production d'acide (méth)acrylique
Isogai et al.	2005	CONTRIBUTING FACTOR ANALYSIS AND ITS APPLICATION FOR AN ALCOHOL PLANT REBOILER FOULING PHENOMENA
BR112019015152A2 (pt)	2020-03-24	Método para preparar (met)acrilato de norbornila reagindo norborneno com ácido (met)acrílico na presença de trifluoreto de boro como catalisador.
JPH1160555A (ja)	1999-03-02	マレイミド類蒸留残渣の処理方法